Production of hydroxymethylfurfural from levoglucosenone

Abstract

Disclosed are processes comprising contacting an aqueous reaction mixture having an initial pH between about 3 and about 6 and comprising levoglucosenone with a catalyst, and heating the reaction mixture to form a product mixture comprising 5-hydroxymethyl-2-furfural. The processes may further comprise heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst to form a second product mixture comprising one or more of 2,5-furandimethanol, tetrahydrofuran 2,5-dimethanol, 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol.

What is claimed is: 
     
       1. A process comprising:
 a) contacting an aqueous reaction mixture comprising levoglucosenone with a catalyst, wherein the initial pH of the reaction mixture is between about 3 and about 6, and 
 b) heating the reaction mixture at a temperature between about 120° C. and about 200° C. at a pressure of ambient pressure to about 1000 psi for a time sufficient to form a product mixture comprising 5-hydroxymethyl-2-furfural. 
 
     
     
       2. The process of  claim 1 , wherein the concentration of levoglucosenone is between about 1 wt % and about 50 wt %. 
     
     
       3. The process of  claim 1 , wherein the temperature is between about 120° C. and about 150° C. 
     
     
       4. The process of  claim 1 , wherein the pH is between about 3 and about 4. 
     
     
       5. The process of  claim 1 , wherein the catalyst is an acid catalyst. 
     
     
       6. The process of  claim 1 , wherein the catalyst is selected from the group consisting of glycolic acid, levulinic acid, benzoic acid, tungstic acid, and phosphotungstic acid hydrate. 
     
     
       7. The process of  claim 1 , wherein the catalyst is selected from the group consisting of sulfonic acid cation exchange resins, zeolite Y, montmorillonite, H-mordenite, and tungsten oxide. 
     
     
       8. The process of  claim 1 , wherein the catalyst comprises sulfonic acid cation exchange resins, zeolite Y, or phosphotungstic acid, the pH is between about 3 and about 4, and the temperature is about 150° C. 
     
     
       9. The process of  claim 1 , further comprising:
 c) heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a first hydrogenation catalyst at a temperature between about ambient temperature and about 120° C. at a pressure of about ambient pressure to about 1000 psi to form a second product mixture comprising one or more of 2,5-furandimethanol and tetrahydrofuran-2,5-dimethanol; 
 d) separating the second product mixture from the first hydrogenation catalyst; and 
 e) reacting the second product mixture with hydrogen in the presence of a second hydrogenation catalyst at a temperature between about 120° C. and about 260° C. at a pressure of about 800 psi to about 2000 psi to form a third product mixture comprising one or more of 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol. 
 
     
     
       10. The process of  claim 9 , wherein the first hydrogenation catalyst comprises one or more of supported nickel catalysts, catalysts derived from nickel-aluminum alloys, catalysts derived from cobalt-aluminum alloys, supported ruthenium catalysts, supported rhodium catalysts, supported platinum catalysts, and supported palladium catalysts. 
     
     
       11. The process of  claim 9 , wherein the second hydrogenation catalyst comprises one or more of copper catalysts, supported platinum/tungsten catalysts, supported platinum catalysts, and supported palladium catalysts. 
     
     
       12. The process of  claim 1 , further comprising:
 c) heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst at a temperature between about ambient temperature and 120° C. at a pressure of about ambient pressure to about 1000 psi for a time period of 10 minutes to 10 hours, and then at a temperature between about 120° C. and about 260° C. at a pressure of 800 psi to about 2000 psi for a sufficient time to form a second product mixture comprising one or more of 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol. 
 
     
     
       13. The process of  claim 12 , wherein the hydrogenation catalyst comprises one or more of copper catalysts, supported platinum/tungsten catalysts, supported platinum catalysts, and supported palladium catalysts.